Menu

Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 994 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $54.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • Hawaii
  • Superb994 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $54.99
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 572 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • Hawaii
  • Superb572 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 39 reviews)

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start your adventure at Turtle Canyon, where you c... More

Free Cancellation
Start From $119.00
 
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • Hawaii
  • Superb39 reviews5

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adv....

    Free Cancellation
    Start From $119.00
 
 

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

(4.9 of 120 reviews)

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More

Free Cancellation
Start From $163.20
 
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

  • Hawaii
  • Superb120 reviews4.9

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....

    Free Cancellation
    Start From $163.20
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 854 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb854 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $213.41
 
 

Paragon Lahaina Sunset Sail

(4.9 of 28 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Free Cancellation
Start From $102.00
 
Paragon Lahaina Sunset Sail

Paragon Lahaina Sunset Sail

  • Hawaii
  • Superb28 reviews4.9

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Free Cancellation
    Start From $102.00
 
 
-10% Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 415 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Special Offer
Free Cancellation
Start From $143.10
(Saving 10% ) $159.00
 
-10% Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • Hawaii
  • Superb415 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Special Offer
    Free Cancellation
    Start From $143.10
    (Saving 10% ) $159.00
 
 
-inf% Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

(4.5 of 24 reviews)

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More

Special Offer
Free Cancellation
Start From $59.95
(Saving inf% ) $0.00
 
-inf% Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

  • Hawaii
  • Exellent24 reviews4.5

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....

    Special Offer
    Free Cancellation
    Start From $59.95
    (Saving inf% ) $0.00
 
 
-inf% Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 60 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Special Offer
Free Cancellation
Start From $289.00
(Saving inf% ) $0.00
 
-inf% Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb60 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Special Offer
    Free Cancellation
    Start From $289.00
    (Saving inf% ) $0.00
 
 
-15% Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.5 of 37 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Special Offer
Free Cancellation
Start From $101.95
(Saving 15% ) $119.95
 
-15% Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • Hawaii
  • Exellent37 reviews4.5

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Special Offer
    Free Cancellation
    Start From $101.95
    (Saving 15% ) $119.95
 
 
-inf% Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

(4.9 of 31 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Special Offer
Free Cancellation
Start From $203.16
(Saving inf% ) $0.00
 
-inf% Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

  • Hawaii
  • Superb31 reviews4.9

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Special Offer
    Free Cancellation
    Start From $203.16
    (Saving inf% ) $0.00
 
 
-inf% Day's End Cocktail Sunset Sail

Day's End Cocktail Sunset Sail

(4.7 of 95 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More

Special Offer
Free Cancellation
Start From $159.00
(Saving inf% ) $0.00
 
-inf% Day's End Cocktail Sunset Sail

Day's End Cocktail Sunset Sail

  • Hawaii
  • Superb95 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Special Offer
    Free Cancellation
    Start From $159.00
    (Saving inf% ) $0.00
 
 
-15% Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.3 of 47 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Special Offer
Free Cancellation
Start From $93.45
(Saving 15% ) $109.95
 
-15% Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Hawaii
  • Exellent47 reviews4.3

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Special Offer
    Free Cancellation
    Start From $93.45
    (Saving 15% ) $109.95
 
 
-inf% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 316 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Special Offer
Free Cancellation
Start From $72.96
(Saving inf% ) $0.00
 
-inf% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb316 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Special Offer
    Free Cancellation
    Start From $72.96
    (Saving inf% ) $0.00
 
 
-inf% Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 576 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Special Offer
Free Cancellation
Start From $178.72
(Saving inf% ) $0.00
 
-inf% Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb576 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Special Offer
    Free Cancellation
    Start From $178.72
    (Saving inf% ) $0.00
 
 
-inf% Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 130 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Special Offer
Free Cancellation
Start From $249.00
(Saving inf% ) $0.00
 
-inf% Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb130 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Special Offer
    Free Cancellation
    Start From $249.00
    (Saving inf% ) $0.00
 
 
-inf% Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

(4.8 of 757 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Special Offer
Free Cancellation
Start From $141.03
(Saving inf% ) $0.00
 
-inf% Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb757 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Special Offer
    Free Cancellation
    Start From $141.03
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Cruise from Oahu

Waikiki Sunset Cruise from Oahu

(4.7 of 71 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Special Offer
Free Cancellation
Start From $45.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cruise from Oahu

Waikiki Sunset Cruise from Oahu

  • Hawaii
  • Superb71 reviews4.7

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Special Offer
    Free Cancellation
    Start From $45.00
    (Saving inf% ) $0.00
 
 
-inf% Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 740 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More

Special Offer
Free Cancellation
Start From $135.64
(Saving inf% ) $0.00
 
-inf% Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb740 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Special Offer
    Free Cancellation
    Start From $135.64
    (Saving inf% ) $0.00
 
 
-inf% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

(4.9 of 210 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Special Offer
Free Cancellation
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb210 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Special Offer
    Free Cancellation
    Start From $79.00
    (Saving inf% ) $0.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com